diff --git a/server/index.ts b/server/index.ts
index 0a861396d..de546d29d 100644
--- a/server/index.ts
+++ b/server/index.ts
@@ -25,6 +25,7 @@ import {
 } from "./utils/startup";
 import { checkUpdates } from "./utils/updates";
 import onerror from "./onerror";
+import ShutdownHelper, { ShutdownOrder } from "./utils/ShutdownHelper";
 
 // The default is to run all services to make development and OSS installations
 // easier to deal with. Separate services are only needed at scale.
@@ -71,7 +72,8 @@ async function start(id: number, disconnect: () => void) {
   const server = stoppable(
     useHTTPS
       ? https.createServer(ssl, app.callback())
-      : http.createServer(app.callback())
+      : http.createServer(app.callback()),
+    ShutdownHelper.connectionGraceTimeout
   );
   const router = new Router();
 
@@ -120,14 +122,26 @@ async function start(id: number, disconnect: () => void) {
   server.listen(normalizedPortFlag || env.PORT || "3000");
   server.setTimeout(env.REQUEST_TIMEOUT);
 
-  process.once("SIGTERM", shutdown);
-  process.once("SIGINT", shutdown);
+  ShutdownHelper.add("server", ShutdownOrder.last, () => {
+    return new Promise((resolve, reject) => {
+      // Calling stop prevents new connections from being accepted and waits for
+      // existing connections to close for the grace period before forcefully
+      // closing them.
+      server.stop((err, gracefully) => {
+        disconnect();
 
-  function shutdown() {
-    Logger.info("lifecycle", "Stopping server");
-    server.emit("shutdown");
-    server.stop(disconnect);
-  }
+        if (err) {
+          reject(err);
+        } else {
+          resolve(gracefully);
+        }
+      });
+    });
+  });
+
+  // Handle shutdown signals
+  process.once("SIGTERM", () => ShutdownHelper.execute());
+  process.once("SIGINT", () => ShutdownHelper.execute());
 }
 
 throng({
diff --git a/server/logging/Logger.ts b/server/logging/Logger.ts
index caf37c5dc..28b4ceca4 100644
--- a/server/logging/Logger.ts
+++ b/server/logging/Logger.ts
@@ -28,7 +28,9 @@ class Logger {
   output: winston.Logger;
 
   constructor() {
-    this.output = winston.createLogger();
+    this.output = winston.createLogger({
+      level: isProduction ? "info" : "debug",
+    });
     this.output.add(
       new winston.transports.Console({
         format: isProduction
diff --git a/server/logging/Metrics.ts b/server/logging/Metrics.ts
index 56f2bf6f5..1ef053fcf 100644
--- a/server/logging/Metrics.ts
+++ b/server/logging/Metrics.ts
@@ -1,5 +1,6 @@
 import ddMetrics from "datadog-metrics";
 import env from "@server/env";
+import ShutdownHelper, { ShutdownOrder } from "@server/utils/ShutdownHelper";
 
 class Metrics {
   enabled = !!env.DD_API_KEY;
@@ -14,6 +15,8 @@ class Metrics {
       prefix: "outline.",
       defaultTags: [`env:${process.env.DD_ENV ?? env.ENVIRONMENT}`],
     });
+
+    ShutdownHelper.add("metrics", ShutdownOrder.last, () => this.flush());
   }
 
   gauge(key: string, value: number, tags?: string[]): void {
@@ -42,6 +45,16 @@ class Metrics {
 
     return ddMetrics.increment(key);
   }
+
+  flush(): Promise<void> {
+    if (!this.enabled) {
+      return Promise.resolve();
+    }
+
+    return new Promise((resolve, reject) => {
+      ddMetrics.flush(resolve, reject);
+    });
+  }
 }
 
 export default new Metrics();
diff --git a/server/middlewares/rateLimiter.ts b/server/middlewares/rateLimiter.ts
index e64576a83..aaedc3610 100644
--- a/server/middlewares/rateLimiter.ts
+++ b/server/middlewares/rateLimiter.ts
@@ -1,10 +1,10 @@
 import { Context, Next } from "koa";
 import { defaults } from "lodash";
-import RateLimiter from "@server/RateLimiter";
 import env from "@server/env";
 import { RateLimitExceededError } from "@server/errors";
 import Metrics from "@server/logging/Metrics";
 import Redis from "@server/redis";
+import RateLimiter from "@server/utils/RateLimiter";
 
 /**
  * Middleware that limits the number of requests that are allowed within a given
diff --git a/server/routes/api/collections.ts b/server/routes/api/collections.ts
index f3ce9beb5..4299db254 100644
--- a/server/routes/api/collections.ts
+++ b/server/routes/api/collections.ts
@@ -10,7 +10,6 @@ import {
   FileOperationType,
 } from "@shared/types";
 import { colorPalette } from "@shared/utils/collections";
-import { RateLimiterStrategy } from "@server/RateLimiter";
 import collectionExporter from "@server/commands/collectionExporter";
 import teamUpdater from "@server/commands/teamUpdater";
 import { sequelize } from "@server/database/sequelize";
@@ -42,6 +41,7 @@ import {
   presentCollectionGroupMembership,
   presentFileOperation,
 } from "@server/presenters";
+import { RateLimiterStrategy } from "@server/utils/RateLimiter";
 import { collectionIndexing } from "@server/utils/indexing";
 import removeIndexCollision from "@server/utils/removeIndexCollision";
 import {
diff --git a/server/routes/api/documents/documents.ts b/server/routes/api/documents/documents.ts
index d7993bca2..23c8a0eee 100644
--- a/server/routes/api/documents/documents.ts
+++ b/server/routes/api/documents/documents.ts
@@ -7,7 +7,6 @@ import { Op, ScopeOptions, WhereOptions } from "sequelize";
 import { TeamPreference } from "@shared/types";
 import { subtractDate } from "@shared/utils/date";
 import { bytesToHumanReadable } from "@shared/utils/files";
-import { RateLimiterStrategy } from "@server/RateLimiter";
 import documentCreator from "@server/commands/documentCreator";
 import documentImporter from "@server/commands/documentImporter";
 import documentLoader from "@server/commands/documentLoader";
@@ -44,6 +43,7 @@ import {
   presentPolicies,
 } from "@server/presenters";
 import { APIContext } from "@server/types";
+import { RateLimiterStrategy } from "@server/utils/RateLimiter";
 import { getTeamFromContext } from "@server/utils/passport";
 import slugify from "@server/utils/slugify";
 import { assertPresent } from "@server/validation";
diff --git a/server/routes/api/team.ts b/server/routes/api/team.ts
index dd55c8138..73f8cac7b 100644
--- a/server/routes/api/team.ts
+++ b/server/routes/api/team.ts
@@ -1,6 +1,5 @@
 import invariant from "invariant";
 import Router from "koa-router";
-import { RateLimiterStrategy } from "@server/RateLimiter";
 import teamCreator from "@server/commands/teamCreator";
 import teamUpdater from "@server/commands/teamUpdater";
 import { sequelize } from "@server/database/sequelize";
@@ -9,6 +8,7 @@ import { rateLimiter } from "@server/middlewares/rateLimiter";
 import { Event, Team, TeamDomain, User } from "@server/models";
 import { authorize } from "@server/policies";
 import { presentTeam, presentPolicies } from "@server/presenters";
+import { RateLimiterStrategy } from "@server/utils/RateLimiter";
 import { assertUuid } from "@server/validation";
 
 const router = new Router();
diff --git a/server/routes/api/users.ts b/server/routes/api/users.ts
index d5fd4e989..08b6decad 100644
--- a/server/routes/api/users.ts
+++ b/server/routes/api/users.ts
@@ -4,7 +4,6 @@ import { has } from "lodash";
 import { Op, WhereOptions } from "sequelize";
 import { UserPreference } from "@shared/types";
 import { UserValidation } from "@shared/validations";
-import { RateLimiterStrategy } from "@server/RateLimiter";
 import userDemoter from "@server/commands/userDemoter";
 import userDestroyer from "@server/commands/userDestroyer";
 import userInviter from "@server/commands/userInviter";
@@ -25,6 +24,7 @@ import { Event, User, Team } from "@server/models";
 import { UserFlag, UserRole } from "@server/models/User";
 import { can, authorize } from "@server/policies";
 import { presentUser, presentPolicies } from "@server/presenters";
+import { RateLimiterStrategy } from "@server/utils/RateLimiter";
 import {
   assertIn,
   assertSort,
diff --git a/server/routes/api/views.ts b/server/routes/api/views.ts
index 5f2e3bbe6..1937d90e7 100644
--- a/server/routes/api/views.ts
+++ b/server/routes/api/views.ts
@@ -1,10 +1,10 @@
 import Router from "koa-router";
-import { RateLimiterStrategy } from "@server/RateLimiter";
 import auth from "@server/middlewares/authentication";
 import { rateLimiter } from "@server/middlewares/rateLimiter";
 import { View, Document, Event } from "@server/models";
 import { authorize } from "@server/policies";
 import { presentView } from "@server/presenters";
+import { RateLimiterStrategy } from "@server/utils/RateLimiter";
 import { assertUuid } from "@server/validation";
 
 const router = new Router();
diff --git a/server/routes/auth/providers/email.ts b/server/routes/auth/providers/email.ts
index c432ede84..851a93047 100644
--- a/server/routes/auth/providers/email.ts
+++ b/server/routes/auth/providers/email.ts
@@ -2,7 +2,6 @@ import Router from "koa-router";
 import { find } from "lodash";
 import { Client } from "@shared/types";
 import { parseDomain } from "@shared/utils/domains";
-import { RateLimiterStrategy } from "@server/RateLimiter";
 import InviteAcceptedEmail from "@server/emails/templates/InviteAcceptedEmail";
 import SigninEmail from "@server/emails/templates/SigninEmail";
 import WelcomeEmail from "@server/emails/templates/WelcomeEmail";
@@ -10,6 +9,7 @@ import env from "@server/env";
 import { AuthorizationError } from "@server/errors";
 import { rateLimiter } from "@server/middlewares/rateLimiter";
 import { User, Team } from "@server/models";
+import { RateLimiterStrategy } from "@server/utils/RateLimiter";
 import { signIn } from "@server/utils/authentication";
 import { getUserForEmailSigninToken } from "@server/utils/jwt";
 import { assertEmail, assertPresent } from "@server/validation";
diff --git a/server/services/collaboration.ts b/server/services/collaboration.ts
index 353c2bd6b..d446ab6cb 100644
--- a/server/services/collaboration.ts
+++ b/server/services/collaboration.ts
@@ -6,6 +6,7 @@ import Koa from "koa";
 import WebSocket from "ws";
 import { DocumentValidation } from "@shared/validations";
 import Logger from "@server/logging/Logger";
+import ShutdownHelper, { ShutdownOrder } from "@server/utils/ShutdownHelper";
 import AuthenticationExtension from "../collaboration/AuthenticationExtension";
 import LoggerExtension from "../collaboration/LoggerExtension";
 import MetricsExtension from "../collaboration/MetricsExtension";
@@ -79,7 +80,7 @@ export default function init(
     socket.end(`HTTP/1.1 400 Bad Request\r\n`);
   });
 
-  server.on("shutdown", () => {
-    return hocuspocus.destroy();
-  });
+  ShutdownHelper.add("collaboration", ShutdownOrder.normal, () =>
+    hocuspocus.destroy()
+  );
 }
diff --git a/server/services/websockets.ts b/server/services/websockets.ts
index 6643c9f00..a566b9746 100644
--- a/server/services/websockets.ts
+++ b/server/services/websockets.ts
@@ -10,6 +10,7 @@ import * as Tracing from "@server/logging/tracer";
 import { traceFunction } from "@server/logging/tracing";
 import { Document, Collection, View, User } from "@server/models";
 import { can } from "@server/policies";
+import ShutdownHelper, { ShutdownOrder } from "@server/utils/ShutdownHelper";
 import { getUserForJWT } from "@server/utils/jwt";
 import { websocketQueue } from "../queues";
 import WebsocketsProcessor from "../queues/processors/WebsocketsProcessor";
@@ -72,7 +73,7 @@ export default function init(
     socket.end(`HTTP/1.1 400 Bad Request\r\n`);
   });
 
-  server.on("shutdown", () => {
+  ShutdownHelper.add("websockets", ShutdownOrder.normal, async () => {
     Metrics.gaugePerInstance("websockets.count", 0);
   });
 
diff --git a/server/RateLimiter.ts b/server/utils/RateLimiter.ts
similarity index 100%
rename from server/RateLimiter.ts
rename to server/utils/RateLimiter.ts
diff --git a/server/utils/ShutdownHelper.ts b/server/utils/ShutdownHelper.ts
new file mode 100644
index 000000000..a8b553d3f
--- /dev/null
+++ b/server/utils/ShutdownHelper.ts
@@ -0,0 +1,96 @@
+import { groupBy } from "lodash";
+import Logger from "@server/logging/Logger";
+import { timeout } from "./timers";
+
+export enum ShutdownOrder {
+  first = 0,
+  normal = 1,
+  last = 2,
+}
+
+type Handler = {
+  name: string;
+  order: ShutdownOrder;
+  callback: () => Promise<unknown>;
+};
+
+export default class ShutdownHelper {
+  /**
+   * The amount of time to wait for connections to close before forcefully
+   * closing them. This allows for regular HTTP requests to complete but
+   * prevents long running requests from blocking shutdown.
+   */
+  public static readonly connectionGraceTimeout = 5 * 1000;
+
+  /**
+   * The maximum amount of time to wait for ongoing work to finish before
+   * force quitting the process. In the event of a force quit, the process
+   * will exit with a non-zero exit code.
+   */
+  public static readonly forceQuitTimeout = 60 * 1000;
+
+  /** Whether the server is currently shutting down */
+  private static isShuttingDown = false;
+
+  /** List of shutdown handlers to execute */
+  private static handlers: Handler[] = [];
+
+  /**
+   * Add a shutdown handler to be executed when the process is exiting
+   *
+   * @param name The name of the handler
+   * @param callback The callback to execute
+   */
+  public static add(
+    name: string,
+    order: ShutdownOrder,
+    callback: () => Promise<unknown>
+  ) {
+    this.handlers.push({ name, order, callback });
+  }
+
+  /**
+   * Exit the process after all shutdown handlers have completed
+   */
+  public static async execute() {
+    if (this.isShuttingDown) {
+      return;
+    }
+    this.isShuttingDown = true;
+
+    // Start the shutdown timer
+    void timeout(this.forceQuitTimeout).then(() => {
+      Logger.info("lifecycle", "Force quitting");
+      process.exit(1);
+    });
+
+    // Group handlers by order
+    const shutdownGroups = groupBy(this.handlers, "order");
+    const orderedKeys = Object.keys(shutdownGroups).sort();
+
+    // Execute handlers in order
+    for (const key of orderedKeys) {
+      Logger.debug("lifecycle", `Running shutdown group ${key}`);
+      const handlers = shutdownGroups[key];
+
+      await Promise.allSettled(
+        handlers.map(async (handler) => {
+          Logger.debug("lifecycle", `Running shutdown handler ${handler.name}`);
+
+          await handler.callback().catch((error) => {
+            Logger.error(
+              `Error inside shutdown handler ${handler.name}`,
+              error,
+              {
+                name: handler.name,
+              }
+            );
+          });
+        })
+      );
+    }
+
+    Logger.info("lifecycle", "Gracefully quitting");
+    process.exit(0);
+  }
+}
diff --git a/server/utils/queue.ts b/server/utils/queue.ts
index 3442cdbb8..94e70cd10 100644
--- a/server/utils/queue.ts
+++ b/server/utils/queue.ts
@@ -3,6 +3,7 @@ import { snakeCase } from "lodash";
 import env from "@server/env";
 import Metrics from "@server/logging/Metrics";
 import Redis from "../redis";
+import ShutdownHelper, { ShutdownOrder } from "./ShutdownHelper";
 
 export function createQueue(
   name: string,
@@ -57,5 +58,9 @@ export function createQueue(
     }, 5 * 1000);
   }
 
+  ShutdownHelper.add(name, ShutdownOrder.normal, async () => {
+    await queue.close();
+  });
+
   return queue;
 }
diff --git a/server/utils/timers.ts b/server/utils/timers.ts
new file mode 100644
index 000000000..d4ca5da0a
--- /dev/null
+++ b/server/utils/timers.ts
@@ -0,0 +1,8 @@
+/**
+ * Returns a promise that resolves after a specified number of milliseconds.
+ *
+ * @param [delay=1] The number of milliseconds to wait before fulfilling the promise.
+ */
+export function timeout(ms = 1) {
+  return new Promise((resolve) => setTimeout(resolve, ms));
+}